Guesthouse vacation rentals in Kailua
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouse rentals in Kailua
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Kailua guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Hauula
4.87 out of 5 average rating, 87 reviewsOhana Country Cottage
Guesthouse in Haleiwa
4.89 out of 5 average rating, 90 reviewsBeach Cottage w bikes on Sunset Pt
Guesthouse in Haleiwa
4.67 out of 5 average rating, 520 reviews1 block to beach 3 Beds!
Guesthouse in Haleiwa
4.95 out of 5 average rating, 206 reviews1-Bed, 1-Bath - Walk to the Beach
Guesthouse in Honolulu
4.92 out of 5 average rating, 143 reviewsHale Wa’a - 2 bed/2 bath - 5 minute walk to beach!
Guesthouse in Kailua
4.78 out of 5 average rating, 137 reviewsKailua Beach Cottage - 90/TVU-0287
Guesthouse in Haleiwa
4.83 out of 5 average rating, 59 reviewsApril & May special ! Hula House Sunset Pt. bikes
Guest house rentals with a patio
Guesthouse in Waianae
4.93 out of 5 average rating, 58 reviewsMauna 'Olu Ohana Studio
Guesthouse in Kailua
5.0 out of 5 average rating, 3 reviewsLovely Private Kailua Cottage
Guesthouse in Honolulu
4.53 out of 5 average rating, 19 reviewsLife on the Water Hawaii
Guesthouse in Honolulu
Honolulu Paradise Vacation, free parking, WiFi A/C
Guesthouse in Laie
Close 2 Beach Entire Guest Suite
Guesthouse in Kailua
4.89 out of 5 average rating, 18 reviewsKailua's Premier Private Luxury Lofty Bungalow
Guesthouse in Kailua
5.0 out of 5 average rating, 8 reviewsThe Banyan Beach Bungalow
Guest house rentals with a washer and dryer
Guesthouse in Waianae
5.0 out of 5 average rating, 16 reviewsBeautiful Mountain Studio Retreat
Guesthouse in Honolulu
4.85 out of 5 average rating, 75 reviewsManoa Valley Duplex with Mountain and Ocean Views
Guesthouse in Kahuku
4.86 out of 5 average rating, 7 reviewsSpacious King bed studio
Guesthouse in Hauula
5.0 out of 5 average rating, 18 reviewsModern 1 Bed by the Beach w/Stay Discounts
Guesthouse in Ewa Beach
4.95 out of 5 average rating, 350 reviewsPlumeria Resurt at the Beach
Guesthouse in Kapolei
4.94 out of 5 average rating, 93 reviewsAloha Living Near Ko’olina + WiFi/Sleeps 5
Guesthouse in Haleiwa
4.86 out of 5 average rating, 110 reviewsGarden Studio, walk to Sunset Beach, 30 day rental
Guesthouse in Haleiwa
4.88 out of 5 average rating, 33 reviewsTropical Acreage + Fruit Trees + Beach ~5m drive!
Quick stats about guesthouse rentals in Kailua
Total rentals
30 properties
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
30 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Total number of reviews
2.1K reviews
Nightly prices starting at
$90 before taxes and fees
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